(+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile

Base Information

• Chemical Name: (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile
• CAS No.: 159108-94-8
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.283
• Mol file: 159108-94-8.mol

Synonyms:

Chemical Property of (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile

There total 12 articles about (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile (159108-94-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 42 percent / Zn dust / benzene / 1 h / Heating

2: 95 percent / Jones' reagent / acetone / 1 h / 0 °C

3: 92 percent / Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / 1 h / -20 °C

4: 97 percent / pyridine / 4 h / Ambient temperature

5: 8 h / 33 °C / lipase 'Amano A'; phosphate buffer pH 7.25

6: 94 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

7: 97 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

8: 99 percent / KH / tetrahydrofuran / 0.17 h / Ambient temperature

9: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

10: pyridine / 12 h / Ambient temperature

11: dimethylsulfoxide / 12 h / 40 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; jones' reagent; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; potassium hydride; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;

Reference yield:

α,β-syn-methyl 3-hydroxy-2-methyl-3-(p-methoxyphenyl)propionate (17226-85-6,17226-86-7,34880-65-4,119068-85-8,136521-24-9,136521-25-0,136734-11-7) → (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile (159108-94-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / pyridine / 4 h / Ambient temperature

2: 8 h / 33 °C / lipase 'Amano A'; phosphate buffer pH 7.25

3: 94 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

4: 97 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

5: 99 percent / KH / tetrahydrofuran / 0.17 h / Ambient temperature

6: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

7: pyridine / 12 h / Ambient temperature

8: dimethylsulfoxide / 12 h / 40 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; potassium hydride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

methyl 3-(4'-methoxyphenyl)-2-methyl-3-oxopropanoate (86109-34-4) → (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile (159108-94-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / 1 h / -20 °C

2: 97 percent / pyridine / 4 h / Ambient temperature

3: 8 h / 33 °C / lipase 'Amano A'; phosphate buffer pH 7.25

4: 94 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 97 percent / imidazole / dimethylformamide / 0.33 h / 0 °C

6: 99 percent / KH / tetrahydrofuran / 0.17 h / Ambient temperature

7: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

8: pyridine / 12 h / Ambient temperature

9: dimethylsulfoxide / 12 h / 40 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; potassium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

sodium cyanide

4-methoxy-benzaldehyde

α,β-anti-methyl 3-hydroxy-2-methyl-3-(p-methoxyphenyl)propionate

α,β-syn-methyl 3-hydroxy-2-methyl-3-(p-methoxyphenyl)propionate

Downstream raw materials:

(E)-(3S,4R)-6-(4-Chloro-3-methoxy-phenyl)-4-methoxy-3-methyl-hex-5-enoic acid

5-(4'-chloro-5'-methoxyphenyl)-(2S)-methyl-(3R)-methoxy-1-methoxycarbonyl-(4E)-pentene

(E)-(3S,4R)-4-methoxy-6-(4-methoxyphenyl)-3-methylhex-5-enenitrile

5-(4'-chloro-5'-methoxyphenyl)-(2S)-methyl-(3R)-methoxy-1-cyano-(4E)-pentene